General and Selective Copper-Catalyzed Reduction of Tertiary and Secondary Phosphine Oxides: Convenient Synthesis of Phosphines

被引:170
作者
Li, Yuehui [1 ]
Das, Shoubhik [1 ]
Zhou, Shaolin [1 ]
Junge, Kathrin [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
HIGHLY EFFICIENT; ENANTIOSELECTIVE HYDROGENATION; ASYMMETRIC HYDROPHOSPHINATION; STEREOSPECIFIC DEOXYGENATION; SELF-ENCAPSULATION; FUNCTIONAL-GROUP; REDUCING AGENT; LIGANDS; ARYL; SYSTEM;
D O I
10.1021/ja301764m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel catalytic reductions of tertiary and secondary phosphine oxides to phosphines have been developed. Using tetramethyldisiloxane (TMDS) as a mild reducing agent in the presence of copper complexes, PO bonds are selectively reduced in the presence of other reducible functional groups (FGs) such as ketones, esters, and olefins. Based on this transformation, an efficient one pot reduction/phosphination domino sequence allows for the synthesis of a variety of functionalized aromatic and aliphatic phosphines in good yields.
引用
收藏
页码:9727 / 9732
页数:6
相关论文
共 108 条
[1]   Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation [J].
Addis, Daniele ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6004-6011
[2]   Facile synthesis of chelating bisphosphine oxides and bisphosphines via palladium-catalyzed bishydrophosphinylation reactions [J].
Allen, A ;
Ma, L ;
Lin, WB .
TETRAHEDRON LETTERS, 2002, 43 (20) :3707-3710
[3]   An improved cu-based catalyst system for the reactions of alcohols with aryl halides [J].
Altman, Ryan A. ;
Shafir, Alexandr ;
Choi, Alice ;
Lichtor, Phillip A. ;
Buchwald, Stephen L. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :284-286
[4]   (BDP)CuH: A "hot" Stryker's reagent for use in achiral conjugate reductions [J].
Baker, Benjamin A. ;
Bokovic, Zarko V. ;
Lipshutz, Bruce H. .
ORGANIC LETTERS, 2008, 10 (02) :289-292
[5]   AN AIR-STABLE CATALYST SYSTEM FOR THE CONVERSION OF ESTERS TO ALCOHOLS [J].
BERK, SC ;
BUCHWALD, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3751-3753
[6]   Copper-catalyzed synthesis of alkynylphosphine derivatives: unprecedented use of nucleophilic phosphorus compounds [J].
Bernoud, Elise ;
Alayrac, Carole ;
Delacroix, Olivier ;
Gaumont, Annie-Claude .
CHEMICAL COMMUNICATIONS, 2011, 47 (11) :3239-3241
[7]   New perfluoroalkylated BINAP usable as a ligand in homogeneous and supercritical carbon dioxide asymmetric hydrogenation [J].
Berthod, M ;
Mignani, G ;
Lemaire, M .
TETRAHEDRON-ASYMMETRY, 2004, 15 (07) :1121-1126
[8]   4,4′ and 5,5′-DiamBINAP as a hydrosoluble chiral ligand:: syntheses and use in Ru(II) asymmetric biphasic catalytic hydrogenation [J].
Berthod, M ;
Saluzzo, C ;
Mignani, G ;
Lemaire, M .
TETRAHEDRON-ASYMMETRY, 2004, 15 (04) :639-645
[9]   A catalytic method for the reduction of secondary and tertiary phosphine oxides [J].
Berthod, Mikael ;
Favre-Reguillon, Alain ;
Mohamad, Jahjah ;
Mignani, Gerard ;
Docherty, Gordon ;
Lemaire, Marc .
SYNLETT, 2007, (10) :1545-1548
[10]  
Borner A., 2008, Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications